Qtjinazomne compoi



Patented Sept. 4, 1934 users STATES PATENT'oFeFi-ci;

QUINAZOLINE COMPOUNDS Giacomo Maffei, Milan, Italy, assign'oi to the firm' S. A. Ledoga Prodotti ghin ici e Farmaceutioi, Milan, Italy No Drawing. Application lllarchQZ/T, 1930, Serial No. 4395540. In Germany May 30, 1929 V 11 Claims. (or; 2eo a2" is understood that when the salts areproduced, they are splihby the addition of alkali; for in'-;' stance, potassium hydroxide into bases, according to well known methods, in the following ex- A comparatively large number of quaternary ases derive m. u n z l n i own; th orm; elubl sa with or and r ani acids 7 It has now been found, according to this invention, that certain hitherto unknown quaternary bases of substituted dihydroquinazolines of the type 6-R,3 -R-phe y1-) 3',4-di ydrquinaze n in which R may represent an organic aliphatic or aromatic or the like radical, possessimportant physiological actions. The physiological action.

,, aforesaid kind are derivatives of the general formula:

The residue R may consist of H, CHz(methyl) CzH5(ethyl), OCH3(methoxy), OC2H5(ethoxy) or a similar organic radical whilst R represents a member selected from a saturated or unsaturated aliphatic group, for instance, CH3(methy1) CII2CHCHz(al1yl) or the CHzCHzOI-I(hydroxy ethyl) group or a phenyl ester of the latter. If the residue R represents H, i. e. if no substitution has taken place in the 6-position the physiological action only appears when R has at least two carbon atoms. The hydroxy ethyl group in particular imparts a blood pressure-lowering action to the new preparations.

Substituted dihydroquinazolines of the general type 6.R.(4.R-phenyl) -3.4.dihydroquinazoline are employed as starting material. The products are prepared according to the usual methods by converting the said dihydroquinazolines into quaternary bases. Alkylation may, for example, be effected with aliphatic or aromatic halogen derivatives or dimethyl sulphate may be employed. It

amples.

Era p 'es 1. 29.6 parts of 6.ethoxyw-3( iethoxyphenyl) 3.4.dihydroquinazoline are heated for a few hours with 14.19 parts of methyl'iodide and parts of ether to --about140 Czin an autoclave with stirring. The base is then liberated by means of I alkali in the usual manner and extracted from the reaction mixture after which it is crystallized several times fromalcohol. It iorms white crystals having aenelting point 'of 114 C. The structural formula of the'end produtt isf:

2. 23.6 parts of 6.methyl-3.(p-tolyl)-3.4.dihy droquinazoline are heated for a few hours with 12.09 parts of allyl bromide and parts of henzene to about C. to C. in an autoclave with stirring. The base after liberation by means of alkali in the usual manner and extraction is recrystallized from various solvents until it shows a constant melting point of 110 C. The formula of the end product is:

3. 23.6 parts of 6.methyl-3.(p-tolyl) -3.4.dihydroquinazoline are heated for a few hours with 8.05 parts of ethylene chlorhydrine ,to C. to C. The base after liberation by means of alkali in the usual manner and extraction is purified and crystallized as the chlorhydrate until it shows a constant melting point of from 214 C. to 215 C. The formula of the end product is:

What I claim is: 1. Quinazoline compounds of the general type corresponding to the graphic formula in which R is an alkyl or an alkoxy radical and R is an alkyl or a hydroxy alkyl radical or a phenyl ester of the latter.

2. The product of claim l in which R and R are both alkyl radicals.

3. The product of claim 1 in which R is an alkoxy and R an alkyl radical.

4. The product of claim 1 in which R is an alkyl and R a hydroxy ethyl radical.

' ,j5. Quinazoline compounds ofthe general type corresponding to the graphic formula N-O-O 02H:

6. Quinazoline compounds of the general type corresponding to the graphic formula CgHaO emer es,

7. Quinazoli ne compounds of the general type corresponding to the graphic formula 0Q CHzCHaOH 8. A process for preparing quinazoline compounds comprising converting dihydroquinazolines of the general type having the formula GIACOMO MAFFEI. 

